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i-Pr2NMgCl·LiCl Enables the Synthesis of Ketones by Direct Addition of Grignard Reagents to Carboxylate Anions

Kilian Colas, A. Catarina V. D. dos Santos and Abraham Mendoza*

*Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, 106 91 Stockholm, Sweden, Email: abraham.mendozasu.se

K. Colas, A. C. V. D. dos Santos, A. Mendoza, Org. Lett., 2019, 21, 7851-7856.

DOI: 10.1021/acs.orglett.9b02899 (free Supporting Information)


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Abstract

A magnesium amide additive activates and controls the addition of mild Grignard reagents to carboxylate anions and therefore avoids the use of organolithium reagents or activated acyl sources that need to be independently prepared. This strategy enables the modular synthesis of ketones from CO2 and the preparation of isotopically labeled pharmaceutical building blocks in a single operation.

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Key Words

acylation (ketones, aryl ketones), Grignard reaction


ID: J54-Y2019